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Curious as Hell

Curious as Hell

By: Tyler Chisholm
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The podcast where relentless curiosity meets leadership transformation. Hosted by Tyler Chisholm—entrepreneur, CEO, and lifelong learner—Curious as Hell is the go-to podcast for leaders, innovators, and trailblazers who believe that asking the right questions can unlock new possibilities in business and life. In each episode, Tyler sits down with top executives, entrepreneurs, and thought leaders to explore how curiosity fuels innovation, builds stronger teams, and drives personal growth. Whether it's uncovering the leadership strategies behind top-performing companies, unpacking the mindset shifts that foster resilience, or challenging conventional wisdom, Curious as Hell delivers actionable insights that help you lead with confidence and creativity. If you're a growth-minded leader looking for fresh perspectives, practical strategies, and inspiring conversations that push boundaries, then you're in the right place.© 2025 clearmotive marketing group Economics Management Management & Leadership Personal Development Personal Success
Episodes
  • Curious as Hell S01E03: No Grade 11. 170 Investor No's. The Decisions That Built the Company
    Jun 8 2026
    Nobody would hire her. So she listed herself on Kijiji for $22/hour and built a company from that. Nine years later, she was signing exit papers, and she could not tell a single person it was happening, not even her wife. This is the version of that story she could not tell while it was happening.Bobbie Racette founded Virtual Gurus in 2016 after being turned down for every job she applied for as a queer, Indigenous woman in tech. She built it from a Kijiji posting with no grade 11 education and no playbook, through 170 investor rejections, into a VC-backed company she exited nine years later. She is now the chair of Queer Tech and the Indigenous Prosperity Foundation, and is building Tapwi, a FinTech platform for underserved founders named after the Cree word for truth.This conversation does not tell the version of the story that looks good on LinkedIn. It goes into the cost of hiding your identity, the people-pleasing trap that stalls real growth, and what it actually takes to process an exit when you cannot talk about it with anyone.Key themes from this episode:On the risk of certainty: Bobbie admits she was so fixed on where the business was going that she almost missed where it was actually heading. Certainty without curiosity nearly cost her the company.The moment she stopped hiding: A young trans woman showed up at her three-person office after hearing Bobbie on the radio and said she had saved her life. That was the day Bobbie decided to tell her story fully, every time, and everything changed.Building a culture around story: The employees who joined in the final three years of Virtual Gurus were not there for the paycheck. They were there because they had a story, and they felt it was the place where their story would be accepted.The people-pleasing trap: "I tried to make everybody happy versus understand the risks that needed to go. And I think that's where mistakes happen." It was not until Bobbie stopped trying to bring everyone along that the real growth started.Choosing to learn from the exit: She blamed the board, she blamed the new CEO, and then she chose differently. "I could choose to learn, or I could choose to really hate this. And I chose to learn from it."Tapwi and what comes next: Tapwi means truth in Cree. It is a FinTech-style platform for underserved founders, built to give them the resources and honest information Bobbie did not have when she started.Chapters:0:00 — Welcome and Bobbie's story0:50 — "I started Virtual Gurus because nobody would give me a job."1:16 — Queer Tech and the Indigenous Prosperity Foundation2:52 — The financial literacy board game and Walk Together program4:53 — The risk of certainty in the early founder days6:13 — Learning from mistakes before they go too far7:30 — Blind ignorance and brute force: what early founders actually need9:21 — The pivotal realization: the company only grows as much as you do9:49 — The 170 nos and why she stopped hiding her identity11:28 — The radio show, the trans woman, and the moment everything changed13:33 — Building a culture around authenticity and story15:28 — Psychological safety at scale: what leaders carry16:37 — The people-pleasing trap and when growth actually started19:34 — Passing the baton: knowing when it is time to go21:24 — From throwing spaghetti to calculated risks23:46 — What success really looks like versus how it looks on social media25:58 — The dual track: raise or sell, stepping into a president role28:25 — The hardest part of the exit: not being able to tell the team29:47 — Blaming the board, then choosing to learn instead31:07 — Self-help books, ceremony, and digging deeper33:17 — The last eight months: the hardest period34:23 — Money as trauma in the Indigenous world37:14 — The bias leaders carry: the belief that you're always right38:13 — Coaching vs. correcting: helping people shine41:42 — Leading up and leading down: the hardest leadership challenge45:16 — Knowing when you're no longer the right fit47:00 — The journey of self and losing the passion48:10 — Non-negotiables for the next venture50:28 — Boundaries: learning to say no52:23 — Not a victim: owning the exit completely53:36 — Tapwi: truth in Cree, and what she's building next56:11 — The book and the documentary58:29 — What Bobbie is most curious about nowConnect with Bobbie: linkedin.com/in/bobbiejoracetteLearn more about what we do at clearmotive.ca If this conversation was worth your time, subscribe wherever you listen and leave a review. It takes two minutes, and it helps more people find the show. ★ Support this podcast ★
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    1 hr
  • Curious as Hell S01E05: The Leader With the Fewest Blind Spots Wins. Not the Smartest. Here's Why.
    Jun 8 2026

    The skills that got you promoted are the same ones quietly strangling your team's potential.


    Jayson Krause spent eight years as a funded national team bobsled athlete before discovering that the most important performance arena is not a track. It is the room where a senior leader decides whether to solve a problem or ask a question. Since 2010, he has worked with CEOs, founders, and senior executives across Canada and the US, and his message is consistent: curiosity is not a soft skill. It is an operational discipline with a measurable ROI.


    This conversation goes directly at the habits, reward systems, and hidden costs that keep smart leaders stuck, and the framework for getting unstuck.

    Key themes from this episode:

    • The three triggers that bring leaders to coaching: the board mandate, the proactive edge-seeker, and the nightmare that wakes you up at 2 am. Mandated coaching rarely works. Pain is what actually creates space for real change.
    • The Awareness, Intention, Experiment, Reflection (A-I-E-R) model: how to move from reaction to reflection before you blow it, borrowed from elite sport and applied directly to leadership behaviour.
    • The seduction of solving: every time you answer a question your team could have answered themselves, you get a dopamine hit and they lose a development opportunity. The habit is well-intentioned and quietly destructive.
    • Relational equity: your engagement problem is not a culture problem. It is a measurement problem. Jayson explains what to track instead.
    • The meerkat story: a COO described by his team as the Grim Reaper rebuilt his entire reputation in six months through deliberate, specific work. This is what that actually looks like.
    • What happens when you ask your team "What would make this the best year of your professional career?" and actually wait for the answer: most leaders have never asked it. Most teams have never been asked.

    Chapters:

    • 0:00 — Introduction
    • 1:29 — Jayson's path: from national team athlete to executive coach
    • 3:57 — Coaching without having been there: the asset nobody talks about
    • 6:18 — The three triggers for coaching
    • 9:32 — Why leaders default to tactics over self-awareness
    • 11:56 — The question every leader needs to sit with
    • 13:41 — "Subtle is significant": the bobsled lesson that changes how you run a team
    • 19:01 — How values get weaponized — and what to do before it happens
    • 22:14 — The AIER model: awareness, intention, experiment, reflection
    • 27:35 — The dopamine trap: why you keep solving problems that aren't yours to solve
    • 33:09 — The risk of certainty (and the illusion hiding inside it)
    • 40:27 — The CFO who became the Grim Reaper — and then became a meerkat
    • 49:05 — Relational equity: the only engagement metric that actually matters
    • 54:29 — Joe's story: what happens when a leader refuses the narrative
    • 1:03:15 — The skin-covered Petri dish: why the leader's culture is always ground zero
    • 1:09:02 — Canada vs. the US: same humans, different appetite for investment
    • 1:11:16 — Jayson's parting challenge

    Connect with Jayson Krause: linkedin.com/in/jayson-krause


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    1 hr and 13 mins
  • Curious as Hell S01E07: Retain Better. Burn Out Less. Build Teams That Don't Need You in Every Room.
    Jun 8 2026

    Season one of Curious as Hell asked one question: What does it really mean to lead today? Over six conversations, a pattern kept emerging. The leaders who were doing it well weren't the most credentialed or the most certain. They were the ones who had stopped pretending they had all the answers.


    In this final episode of Season 1, Tyler is joined by Meghan, a PhD in Industrial/Organizational Psychology and the founder of Pebble, who steps in as co-host to help unpack what the season's guests were really saying. Together they work through three themes: Curiosity, Not Expertise; Relational and Co-Created; and Growth Through Reflection.


    Part 1: Curiosity, Not Expertise


    The guests who led best had learned, sometimes painfully, to stop leading from what they knew and start leading from what they were willing to find out. Tyler shares the 360 feedback that first cracked open his own leadership. Bobbie Racette talks about the tunnel vision of a startup founder who was moving one direction while the business quietly went another. Iggy Domagalski looks back at the opinions he confused for facts. Lara Murphy unpacks the real difference between asking for help and just delegating work.


    Meghan brings the research lens: why do leaders cling to expertise even when it is clearly not working? Part of it is identity. When you got promoted because you were the best at something, letting go of that thing can feel like letting go of the reason you are in the room. What you have instead of expertise, she argues, is the people around you. That is the resource.


    Part 2: Relational and Co-Created


    Jennifer Lussier's team made "Vote for Jen" stickers when she was interviewing for the CEO role she had been filling as interim. That story, Tyler says, does not require an engagement survey to interpret. Meghan builds on it: the research keeps pointing to the same thing, that the relationship with your manager is the primary driver of whether someone stays, contributes, or quietly leaves. Jayson Krause calls it relational equity and argues that most organizations are measuring the wrong thing entirely.


    Lara Murphy shares the moment her team told her to go prep for a big presentation instead of joining the call. She did not need to be in the room. The team had it. Tyler and Meghan argue that this is what letting go actually looks like in practice. And then the harder version: what do you do when your door is always open but no one ever walks through it? Meghan is direct: that is a cop-out. Leadership is not waiting for people to come to you. It means walking out of your own door first.


    Part 3: Growth Through Reflection


    This section starts with Iggy Domagalski and his think day: a few hours at Starbucks, phone off, handwritten notes, specific problems on paper. No laptop. Just tea and uninterrupted thinking time. Meghan connects it to the research on sustained high performance. The leaders who do not burn out tend to have what she calls an "other world," something completely separate from work that creates a flow state: a tango dancer, a clarinet player, a tractor on a rural property.


    Bobbie Racette talks about what it took to stop being the victim of an acquisition and choose to learn from it instead. Three or four months of sitting with it before the reframe clicked. Tyler connects it to what Meghan's PhD research keeps returning to: the interior condition of the leader is the foundation on which everything else is built.


    Jayson Krause closes it out with the AIER framework: a cycle that starts with awareness and moves through intention, experiment, and reflection. It is the operating system of a leader who is actually growing instead of just grinding.


    This is the episode to start with if you have not listened yet. And it is the episode to come back to once you have.


    Connect with Meghan Donahoe, PhD (ABD), founder of Pebble.

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    1 hr and 56 mins
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